16312-21-3

Basic information

• Product Name: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE
• Synonyms: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE
• CAS NO: 16312-21-3
• Molecular Formula: C₄H₅NO₂S
• Molecular Weight: 131.15
• Mol File: 16312-21-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 40-43°C
• Boiling Point: 204.7°Cat760mmHg
• Flash Point: 77.6°C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 0.26mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.27±0.20(Predicted)
• CAS DataBase Reference: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE(16312-21-3)
• EPA Substance Registry System: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE(16312-21-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16312-21-3(Hazardous Substances Data)

Usage

Uses

3-methyl-1,3-thiazolidine-2,4-dione can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

To a solution of 2,4-thiazolidinedione (1 equiv) in 5 mL of DMF was added potassium carbonate (1.1 equiv) and halogen (1.1 equiv). The suspension was stirred at 80 oC overnight. Solvent was evaporated and the residue was purified by flash column chromatography ( petroleum ether/EtOAc, 5:1) to afford the product 3. 3-Methylthiazolidine-2,4-dione (3a) Following the previous procedure, 2,4-thiazolidinedione (500 mg, 4.3 mmol) and iodomethane (0.3 mL, 4.7 mmol). 3a as white solid (460 mg, 82%).

InChI:InChI=1/C4H5NO2S/c1-5-3(6)2-8-4(5)7/h2H2,1H3

Upstream product

• 598-52-7 1-(methyl)-thiourea 
• 79-11-8 chloroacetic acid 
• 598-21-0 2-Bromoacetyl bromide 
• 2295-31-0 thiazoline-2,4-dione 
• 77-78-1 dimethyl sulfate 
• 39131-10-7 1,3-thiazolidine-2,4-dione potassium salt 
• 1239279-47-0 C₁₆H₁₄BrN₃O₄S₂ 
• 1239279-42-5 C₁₆H₁₄BrN₃O₅S 
• 74-88-4 methyl iodide 
• 65645-28-5 methyl-thiocarbamic acid O-menthyl ester 
• 79-08-3 bromoacetic acid 
• 71-43-2 benzene 
• 114710-77-9 3-Methyl-2-[(Z)-pyridin-2-ylimino]-thiazolidin-4-one 
• 37929-27-4 1,4,4,6-tetramethyl-1,4-dihydropyrimidine-2(3H)-thione 

Downstream Products

• 2365-48-2 Methyl thioglycolate 
• 68-11-1 mercaptoacetic acid 
• 74-89-5 methylamine 
• 365989-89-5 C₁₃H₁₀N₂O₂S 
• 5272-47-9 5-[1-Dimethylamino-meth-(E)-ylidene]-3-methyl-thiazolidine-2,4-dione 

Relevant articles and documents

Design, synthesis,: In silico molecular modelling studies and biological evaluation of novel indole-thiazolidinedione hybrid analogues as potential pancreatic lipase inhibitors

Pancreatic lipase (PL) is a key enzyme responsible for the digestion of dietary triglycerides; hence its inhibition is considered as a promising target for the management and/or treatment of obesity. A new series of indole-thiazolidinedione (TZD) hybrid analogues were synthesized using a molecular hybridisation approach and evaluated for their anti-obesity effects via PL inhibition. The targeted analogues were synthesized via the condensation reaction between various substituted isatin with TZD in the presence of aqueous KOH in methanol. Amongst the synthesized analogues, 7k and 7m exhibited a potential PL inhibitory activity (IC50-7.30 and 9.51 μM, respectively). Kinetic study of these potent analogues revealed their competitive mode of enzyme inhibition. This fact was confirmed via fluorescence spectroscopy which further suggested the presence of one binding site for the synthesized analogues. Molecular docking of the synthesized analogues was performed using human PL (PDB ID: 1LPB). The obtained MolDock scores were aligned with the in vitro PL inhibitory activity (Pearson's r = 0.9108, p 0.05). Moreover, a stable conformation of the 1LPB-ligands suggested the stability of these complexes in the dynamic environment. These studies provided a basis for the potential role of the indole-TZD hybrids in PL inhibition and further optimization might result in the development of new lead candidates for obesity treatment.

Design, synthesis and biological evaluation of novel 6-phenyl-1,3a,4,10b-tetrahydro-2H-benzo[c]thiazolo[4,5-e]azepin-2-one derivatives as potential BRD4 inhibitors

Bromodomain-containing protein 4 (BRD4) is a key epigenetic regulator in cancer, and inhibitors targeting BRD4 exhibit great anticancer activity. By replacing the methyltriazole ring of the BRD4 inhibitor I-BET-762 with an N-methylthiazolidone heterocyclic ring, fifteen novel BRD4 inhibitors were designed and synthesized. Compound 13f had a hydrophobic acetylcyclopentanyl side chain, showing the most potent BRD4 inhibitory activity in the BRD4-BD1 inhibition assay (IC50 value of 110 nM), it also significantly suppressed the proliferation of MV-4-11 cells with high BRD4 level (IC50 value of 0.42 μM). Furthermore, the potent apoptosis-promoting and G0/G1 cycle-arresting activity of compound 13f were indicated by flow cytometry. As the downstream-protein of BRD4, c-Myc was in significantly low expression by compound 13f treatment in a dose-dependent manner. All the findings supported that this novel compound 13f provided a perspective for developing effective BRD4 inhibitors.

cGAS ANTAGONIST COMPOUNDS

Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.